Modelling cetrimonium micelles as 4-OH cinnamate carriers targeting a hydrated iron oxide surface

Puelles, Jhonatan Soto; Ghorbani, Mahdi; Crawford, Simon; Ackland, Leigh; Chen, Fang Fang; Somers, Anthony; Forsyth, Maria

doi:10.1016/j.jcis.2021.11.139

Cited by 4 publications

(6 citation statements)

References 59 publications

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“…On the other hand, the CTA cation diffusion continues to decrease, which is consistent with growing micellar size and possibly the lack of any substantial association between the CTA micelle and the anion. Along with the lack of passive film formation in this system, the data suggests that the passivation observed in the PP measurements for CTA-4OHcinn in the absence of ethanol and in the ethanol containing CTA-4EtOcinn is related to a synergy between the two ionic species codelivered to the metal surface as also discussed by us in the previous work …”

Section: Resultssupporting

confidence: 79%

“…In our previous pape,r 4 we found that CTA-4OHcinn micelles form in solution, and the performance of the inhibitor is related to the structure of the micelles. This has been further studied by Soto Puelles 27 and his co-workers via Molecular Dynamics (MD) simulations and Cryo-TEM imaging. Below, we make use of pfg NMR and molecular modeling to understand the inhibitor concentration effect on micellar structure.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Along with the lack of passive film formation in this system, the data suggests that the passivation observed in the PP measurements for CTA-4OHcinn in the absence of ethanol and in the ethanol containing CTA-4EtOcinn is related to a synergy between the two ionic species codelivered to the metal surface as also discussed by us in the previous work. 39 By replacing the H atom in the hydroxyl group of the 4OHcinn anion with an ethyl group to form 4EtOcinn, the hydrogen bonding interactions with the ethanol decrease and stronger interactions are favored between the CTA + cations, thereby leading to entrapment of the 4EtOcinn anion by the cetrimonium micelle. The viscosity data shown in Figure 4d for each of the systems further supports these hypotheses; the addition of ethanol to CTA-4OHcinn leads to an overall increase of the viscosity; however, this is simply because ethanol solutions are more viscous than the aqueous systems alone (note that 6.5% ethanol in water has a higher viscosity, 1.30 Pa•s, than only water, at 1.05 mPa•s).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Engineering Advanced Environmentally Friendly Corrosion Inhibitors, Their Mechanisms, and Biological Effects in Live Zebrafish Embryos

Ghorbani

Puelles

Forsyth

et al. 2022

ACS Sustainable Chem. Eng.

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Carbon steel is one of the most used construction materials and makes up the bulk of steel production in the world. However, this alloy is vulnerable to corrosion, which reduces its safety and costs trillions of dollars worldwide in terms of corrosion protection and infrastructure maintenance. Corrosion inhibitors are among the cheapest and most effective methods to minimize corrosion and maximize the shelf life of this ubiquitous alloy; however, they are often harmful to the environment. Currently there are no reports in terms of engineering design methodology to develop highly effective, advanced corrosion inhibitors. The possible synergistic behavior of a surfaceactive quaternary ammonium with a tailored carboxylate compound provides a rational molecular design toward delivering corrosion inhibitors to a metal surface through controlled speciation in solution. Here we show how entrapment and delivery of the anion inhibitor through speciation and micellar formation can lead to high inhibition efficiency, as determined by potentiodynamic polarization and electrochemical impedance spectroscopy. In particular, we demonstrate how NMR spectroscopy, pfg NMR diffusion measurements, and Cryo-TEM, taken together with molecular dynamic simulations, can reveal the micellar formation and its concentration dependence, with wormlike micelles evident at higher concentrations correlating with a dramatic increase in viscosity. This new organic corrosion inhibitor, cetrimonium 4-ethoxy cinnamate, provides significantly higher corrosion inhibition efficiency compared with the 4-hydroxy cinnamate analogue and with reduced toxic impact in the zebrafish embryo compared to the surface active CTAB often used as an antimicrobial.

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Section: Resultssupporting

confidence: 79%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Engineering Advanced Environmentally Friendly Corrosion Inhibitors, Their Mechanisms, and Biological Effects in Live Zebrafish Embryos

Ghorbani

Puelles

Forsyth

et al. 2022

ACS Sustainable Chem. Eng.

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“…Previous experimental and modelling studies have shown that CTA-4OHcinn forms distinct micelles where the 4-OH cinnamate anions are integrated within the cetrimonium micelles in an oriented way with their carboxylates located in the outer shell and their hydroxyls deeper inside the micelle 25 , 26 . Therefore, to study the effect of 4OH cinnamate on membrane disruption, a CTA-4OHcinn micelle was simulated above a mixed bilayer with a similar composition to the previous bilayer; i.e.…”

Section: Resultsmentioning

confidence: 99%

“…S-5 . Regarding 4-OH cinnamate, a bottom-up approach was adopted for constructing its parameters beginning from all-atom parameters previously published 26 . A detailed discussion and validation of the 4-OH cinnamate CG model can be found in S.I ., Figs.…”

Section: Methodsmentioning

confidence: 99%

Effect of cetrimonium carrier micelles on bacterial membranes and extracellular DNA, an in silico study

Puelles

Ghorbani

Tuck

et al. 2023

Sci Rep

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Microorganisms do not live as dispersed single cells but rather they form aggregates with extracellular polymeric substances at interfaces. Biofilms are considered efficient life forms because they shield bacteria from biocides and collect dilute nutrients. This is a big concern in industry since the microorganisms can colonize a wide range of surfaces, accelerating material deterioration, colonizing medical devices, contaminating ultrapure drinking water, increasing energy costs and creating focus of infection. Conventional biocides that target a specific component of the bacteria are not effective in the presence of biofilms. Efficient biofilm inhibitors are based on a multitarget approach interacting with the bacteria and the biofilm matrix. Their rationale design requires a thorough understanding of inhibitory mechanisms that are still largely lacking today. Herein we uncover via molecular modelling the inhibition mechanism of cetrimonium 4-OH cinnamate (CTA-4OHcinn). Simulations show that CTA-4OH micelles can disrupt symmetric and asymmetric bilayers, representative of inner and outer bacterial membranes, following three stages: adsorption, assimilation, and defect formation. The main driving force for micellar attack is electrostatic interactions. In addition to disrupting the bilayers, the micelles work as carriers facilitating the trapping of 4OH cinnamate anions within the bilayer upper leaflet and overcoming electrostatic repulsion. The micelles also interact with extracellular DNA (e-DNA), which is one of the main components of biofilms. It is observed that CTA-4OHcinn forms spherical micelles on the DNA backbone; which hinders their ability to pack. This is demonstrated by modelling the DNA along the hbb histone-like protein, showing that in the presence of CTA-4OHcinn, DNA does not pack properly around hbb. The abilities of CTA-4OHcinn to cause cell death through membrane disruption and to disperse a mature, multi-species biofilm are also confirmed experimentally.

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Corrosion inhibition mechanism of imidazole ionic liquids with high temperature in 20% HCl solution

et al. 2022

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Modelling cetrimonium micelles as 4-OH cinnamate carriers targeting a hydrated iron oxide surface

Cited by 4 publications

References 59 publications

Engineering Advanced Environmentally Friendly Corrosion Inhibitors, Their Mechanisms, and Biological Effects in Live Zebrafish Embryos

Engineering Advanced Environmentally Friendly Corrosion Inhibitors, Their Mechanisms, and Biological Effects in Live Zebrafish Embryos

Effect of cetrimonium carrier micelles on bacterial membranes and extracellular DNA, an in silico study

Corrosion inhibition mechanism of imidazole ionic liquids with high temperature in 20% HCl solution

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